Mild, efficient and selective silver carbonate mediated O-alkylation of 4-hydroxy-2-quinolones: Synthesis of 2,4-dialkoxyquinolines

Synlett

Volumn , Issue 18, 2005, Pages 2755-2758

  Morel, Ademir Farias ^a   Larghi, Enrique L ^b   Selvero, Marcel Manke ^a  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

^b Universidad Nacional de Rosario   (Argentina)

Author keywords

2,4 dialkoxyquinolines; 4 hydroxy 2 quinolones; Alkylation; Silver carbonate

Indexed keywords

BENZENE; BENZYL BROMIDE; CARBONIC ACID DERIVATIVE; IODINE DERIVATIVE; QUINOLINE DERIVATIVE; QUINOLONE DERIVATIVE; SILVER CARBONATE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL COMPOSITION; QUANTUM YIELD; ROOM TEMPERATURE; SYNTHESIS;

EID: 27844534847     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-918945     Document Type: Article

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45. 3 (2 mmol) under an Argon atmosphere and the resulting slurry was homogenized by magnetic stirring at r.t. for 5 min, giving a yellowish suspension. Then, the halide (4 mmol) was added dropwise to the suspension and the mixture was further stirred at r.t. for 3 d in the dark. After this period the suspension was diluted with EtOAc, filtered through Celite, and the remaining greenish solid was washed 5 times with small portions of EtOAc. After evaporation of the volatiles, the product was isolated by silica gel (230-400 mesh) column chromatography, eluting with mixtures of hexanes and EtOAc.
46. + + H].